2(3H)-Furanone, 3-(triphenylphosphoranylidene)- → alpha-[3-(2,4-Difluorophenoxy)-4-(methanesulfonamido)benzylidene]-gamma-butyrolactone

HRID 1607692Notes

Reaction equation

[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:16]=[C:15]([CH:17]=O)[CH:14]=[CH:13][C:6]=1[NH:7][S:8]([CH2:11]C)(=[O:10])=[O:9].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:31]2[CH2:36][CH2:35][O:34][C:32]2=[O:33])C=CC=CC=1>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[CH:16]=[C:15]([CH:14]=[CH:13][C:6]=1[NH:7][S:8]([CH3:11])(=[O:10])=[O:9])[CH:17]=[C:31]1[CH2:36][CH2:35][O:34][C:32]1=[O:33]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2'-(2,4-difluorophenoxy)-4'-formylethanesulfonanilide (2 g) and α-triphenylphosphoranylidene-γ-butyrolactone (2.2 g) in dimethyl sulfoxide (10 ml) was stirred at 80° C. for 6 hours. The mixture was dissolved in ethyl acetate, and the resulting mixture was washed with water, dried, and concentrated to dryness. The residue was purified by column chromatography on acetate (1:1) to give a powder of α-[3-(2,4-difluorophenoxy)-4-(methanesulfonamido)benzylidene]-γ-butyrolactone (1.7 g).

Workup

washthe resulting mixture was washed with water
customdried
concentrationconcentrated to dryness
customThe residue was purified by column chromatography on acetate (1:1)

Sources & evidence

ORD record: ord-ed61e02bcb2746d29f44c74a925e8903
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04866091

Reaction notes

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